Hydrochloric Acid → 3,4-Dimethoxyphenyl 2-thiazolyl ketone

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Reaction Conditions

Reaction Steps

A hexane solution of butyllithium (9.50 mM) was dissolved in dried diethyl ether (6.5 ml) and cooled to −78° C. A solution of 2-bromothiazole (1.03 g, 6.13 mM) in diethyl ether (0.5 ml) was dropped into this solution. The solution was stirred at that temperature for 30 minutes, then a solution of 3,4-dimethoxybenzonitrile (1.00 g, 6.13 mM) in diethyl ether (3.0 ml) was added and the resultant mixture stirred for a further 6 hours. 1N Hydrochloric acid (20 ml) was poured into the solution obtained, which was then warmed to room temperature and stirred for 30 minutes, then a saturated sodium hydrogencarbonate solution was added to neutralize the solution and extraction was performed with ethyl acetate. Next, the organic layer was washed with brine and dried over anhydrous magnesium sulfate, then the solvent was removed in vacuo to obtain a dark red solid residue. The residue was purified by flash chromatography (SiO2: eluted by gradient from 50% hexane/methylene chloride to 25% hexane/methylene chloride). The solvent was removed in vacuo and the resultant product was dried to obtain 3,4-dimethoxyphenyl 2-thiazolyl ketone 0.71 g (yield 46.5%) as a red solid.

Provenance & Evidence